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When I coach water polo, one of the first things I tell my team is, “Success doesn't always end with a goal.” Players forget their fundamentals—not to mention teamwork and good sportsmanship—when all they can think about is scoring. In the long run, this actually makes the entire team less effective. I want them to focus on the process instead of obsessing over the end result.
The result does not actually change my central responsibility as a coach. Win or lose, my job is still the same: to facilitate an open and honest analysis of what happened, including what went well and what didn't. Winning a few games doesn't mean the team is done growing.
I have the same thought when mentoring employees at FutureFund, my SaaS company that offers one free fundraising platform for K-12 schools. In each case, I'm pushing people to develop expertise in their field—showing them how to find wins and identify areas for improvement regardless of what results they achieve.
But expertise isn't something that can just be given to you—it's something you earn, which requires the ability to be self-reflective. So, as a business coach or mentor, I don't give answers. Instead, I guide people to find the answers for themselves.
This means that my greatest tool as a mentor is the ability to ask questions. Here are the ones I find most effective.
Related: Be a coach, not a referee – How to be a good mentor and manager from a coaching perspective
“How do you think it went?”
This is one of the first questions I ask when I'm coaching or mentoring someone new. It tells me what a person is able to observe for himself.
Once I know what someone can see for themselves, I better understand the skills and knowledge they are likely to apply to other endeavors. Let's say a water polo player scores his first goal in three games – unless they can tell me what they've started doing differently, I have no way of knowing if it's a fluke or not. But if they can identify tactics that helped them score, I know I can count on them to use again.
Here's another example: when I ask an engineer how fixing a bug went, he might tell me that he thinks it was successful because the bug got fixed. But when I ask them if they went back and looked for the same error in other code, they often say no.
again, results do not always show progress. If you want a better idea of your abilities, ask people to tell you about the journey they went on to achieve those results.
“What would you do differently?”
Once people understand how evaluate themselvesyou can encourage them to make positive changes. After asking someone to reflect on their past performance, I always ask them to think about what they would do differently the next time a similar situation arose.
A player may know they were sluggish during a game because they slept poorly the night before – but why weren't they well rested? Did they drink alcohol or stay up too late? If so, would they do these things again before the next game? What do they think might happen if they avoided drinking and got a full eight hours of sleep?
A mentor guides people by answering questions like this and helps them be honest. Just remember, you don't want to seem like you're scolding, which makes people fear judgment and shut them down. Mentoring is not about dictating actions; it's about encouraging people to take ownership of their own growth. This means you need to build trust with people so they feel comfortable opening up with you.
Sometimes, it's helpful if a person's mentor isn't their direct supervisor, but someone who can ask questions from an unbiased place—like an outside consultant. But when you're mentoring one of your employees, I've found the best way to get one honest answer to this question is to demonstrate some vulnerability yourself.
Try to lead by example. Share a story about a similar learning experience you've had so they feel like you're connecting with them rather than putting them under a microscope when you ask questions.
“How have you changed over time?”
Giving immediate feedback after a game or project helps people grow by reflecting on experiences while they're still fresh. But you also want them to be aware of long-term trends in their development – so I always like to ask questions that get people thinking about their performance over time.
If we're playing baseball and I give immediate feedback every time a batter goes up, they'll grow—but I also have to pull them aside at some point and ask them to reflect on their previous 10 at-bats. This helps them spot patterns or habits that go beyond their actions during a single game.
This is also great to help people recognize progress they have arrived after months or years of growth. Some changes take much longer than others – like breaking lifelong habits, attitudes or addictions. Over time, it's easy to get discouraged and feel like incremental change isn't enough anymore—but when someone asks you to look back at who you were when you started, you get a very different sense of how far you've come since then. . . And it can inspire you to keep moving forward.
Mentoring is like that too – ideally, you evolve along with the people you lead or manage. Continue learning how to mentor the people in your life effectively by learning about the different stages of mentoring in the article below.
Related: The Importance of Mentors